1-Methylcyclohexanecarbonyl chloride → HCID 86589904, compound

HRID 2121441Notes

Reaction equation

HRID 2121441 reaction equation
[CH3:1][C:2]1([C:8](Cl)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH:11]1([CH2:17][C@@H:18]([NH2:33])[CH2:19][N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[OH:32])[CH2:22][CH2:21]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C(N(CC)CC)C>[CH:11]1([CH2:17][C@@H:18]([NH:33][C:8]([C:2]2([CH3:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)=[O:9])[CH2:19][N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[OH:32])[CH2:22][CH2:21]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 41892451-Methylcyclohexanecarbonyl chlorideHCID 69738094HCID 69738094, compound

Product 1

HCID 86589904HCID 86589904, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 1-methylcyclohexanecarbonyl chloride, triethylamine and {(1R)-1-cyclohexylmethyl-2-[4-(2-hydroxyphenyl)-piperazin-1-yl]-ethyl}-amine is stirred at 0° C. under a nitrogen atmosphere for 1 hour. The mixture is then concentrated on a rotary evaporator and partitioned between ethyl acetate and saturated aqueous NaHCO3. The combined organic layers are washed with brine, dried and concentrated on a rotary evaporator to yield the desired product, which is purified by chromatography on alumina.

Workup

  1. concentrationThe mixture is then concentrated on a rotary evaporator
  2. custompartitioned between ethyl acetate and saturated aqueous NaHCO3
  3. washThe combined organic layers are washed with brine
  4. customdried
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-90efb62b5d3f4b76be72858a744d6356
Source dataset
uspto-grants-2004_02
Patent number
US06696450B2

Reaction notes

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